Water → HCID 178445635, compound

HRID 726451Notes

Reaction equation

HRID 726451 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[CH3:28][O:29][C:30]([C@H:32]1[CH2:37][CH2:36][C@H:35]([C@H:38]2[CH2:43][CH2:42][C@H:41]([C@H:44]3[CH2:49][CH2:48][C@H:47]([CH2:50][CH2:51][CH:52]=O)[CH2:46][CH2:45]3)[CH2:40][CH2:39]2)[CH2:34][CH2:33]1)=[O:31].O>C1COCC1>[CH3:28][O:29][C:30]([C@H:32]1[CH2:37][CH2:36][C@H:35]([C@H:38]2[CH2:39][CH2:40][C@H:41]([C@H:44]3[CH2:45][CH2:46][C@H:47]([CH2:50][CH2:51][CH:52]=[CH2:2])[CH2:48][CH2:49]3)[CH2:42][CH2:43]2)[CH2:34][CH2:33]1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 178501095HCID 178501095, compound

Product 1

HCID 178445635HCID 178445635, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

A mixture of 130 g (322 mmol) of methyltriphenylphosphonium iodide and 1.3 liters of THF was cooled to -50° C. To this mixture was added 33.4 g (110 mmol) of t-BuOK and the resulting mixture was stirred for one hour. To this mixture was added dropwise, while maintaining a temperature at below -50° C., a solution of 90.0 g (248 mmol) of crude trans-4-(trans-4-(trans-4-(2-formylethyl)-cyclohexyl)cyclohexyl)cyclohexane carboxylic acid methyl ester in 900 ml of THF. After the dropwise addition, the temperature of the reaction solution was gradually allowed to rise up to room temperature and the mixture was stirred for further 5 hours. After the reaction was completed by adding 500 ml of water, the reaction mixture was filtered through Celite, the solvent was distilled off under reduced pressure and the filtrate was extracted with 1.0 liter of toluene. The organic layer was washed three times with 500 ml of water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to a silica gel column chromatography (a developing solvent: toluene) to give 40.0 g of crude trans-4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-cyclohexane carboxylic acid methyl ester.

Workup

  1. additionTo this mixture was added dropwise
  2. temperaturewhile maintaining a temperature at below -50° C.
  3. additionAfter the dropwise addition
  4. customto rise up to room temperature
  5. stirringthe mixture was stirred for further 5 hours
  6. filtrationthe reaction mixture was filtered through Celite
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionthe filtrate was extracted with 1.0 liter of toluene
  9. washThe organic layer was washed three times with 500 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9ca8d8a3cd0e43e89f3fc3b1707de769
Source dataset
uspto-grants-1998_01
Patent number
US05709820

Reaction notes

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